Chlorofluorocarbon (CFC) based chemicals have been widely used in industry in a variety of different applications including as refrigerants, aerosol propellants, blowing agents and solvents, among others. However, certain CFCs are suspected of depleting the Earth's ozone layer. Accordingly, more environmentally friendly substitutes have been introduced as replacements for CFCs. For example, 1,1,1,3,3-pentafluoropropane (HFC-245fa) is recognized as having favorable physical properties for certain industrial applications, such as foam blowing agents and solvents, and therefore is considered to be a good substitute for the CFCs previously used for these applications. Unfortunately, the use of certain hydrofluorocarbons, including HFC-245fa, in industrial applications is now believed to contribute to the global warming. Accordingly, more environmentally friendly substitutes for hydrofluorocarbons are now being sought.
The compound 1-chloro-3,3,3-trifluoropropene, also known as HCFO-1233zd or simply 1233zd, is a candidate for replacing HFC-245fa in some applications, including uses as blowing agents and solvents. 1233zd has a Z-isomer and an E-isomer. Due to differences in the physical properties between these two isomers, pure 1233zd(E), pure 1233zd(Z), or certain mixtures of the two isomers may be suitable for particular applications as refrigerants, propellants, blowing agents, solvents, or for other uses.
The prior art discloses various processes for making HCFO-1233zd. U.S. Pat. No. 5,710,352 discloses a vapor phase process for making 1,1,3,3,3-pentafluoropropane and HCFO-1233zd by reacting 1,1,1,3,3-pentachloropropane (HCC-240fa) with hydrogen fluoride in the presence of a fluorination catalyst. U.S. Pat. No. 6,844,475 discloses a low-temperature liquid phase process for making HCFO-1233zd by reacting 1,1,1,3,3-pentachloropropane (HCC-240fa) with hydrogen fluoride in the presence of a Lewis Acid catalyst or mixture of Lewis Acid catalysts. U.S. Pat. No. 7,829,747 discloses a vapor phase process for making HCFC-1233zd by dehydrofluorinating 3-chloro-1,1,1,3-tetra-fluoropropane (HCFC-244fa) in the presence of a dehydrofluorination catalyst. However, there remains a need for an economic means of producing HCFO-1233zd. The present invention satisfies this need among others. These documents are hereby incorporated herein by reference.